N-aryl-carbamic acid ester-derived and valeric acid ester-derived cross-linkers and conjugates, and methods for their synthesis and use
First Claim
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1. A method of conjugating a first species selected from the group consisting of a protein, a polypeptide, an antibody, a nucleic acid, a small molecule, an aptamer, and a carbohydrate, to a second species selected from the group consisting of a detectable label, a solid phase, a protein, a polypeptide, an antibody, a nucleic acid, a small molecule, an aptamer, and a carbohydrate, the method comprising:
- contacting said first and second species with a crosslinker of the formula;
wherein X is (alkylene oxide)n;
n is between about 40 to about 450; and
Y and Z are independently arylene or heteroarylene units having 5 or 6 ring atoms, optionally substituted with from 1 to 4 substituents independently selected from the group consisting of C1-6 alkyl straight or branched chain, halogen, trihalomethyl, C1-6 alkoxy, —
NO2, —
NH2, —
OH, —
COOR′
, where R′
is H or lower alkyl, —
CH2OH, —
CONH2, and a linkage to a poly(alkylene oxide) moiety, wherein Z is optionally present;
under conditions selected to conjugate said first species to said second species, wherein one of the first or second species becomes covalently bound to said crosslinker through a moiety reactive with an N-hydroxysuccinimide functional group, and the other of the first or second species becomes covalently bound to said crosslinker through a moiety reactive with a maleimide functional group wherein the conjugating step comprises (i) covalent binding of the crosslinker to the first or second species through a moiety reactive with a first functional group that is an N-hydroxysuccinimide or a maleimide functional group, to form a covalently bound crosslinker intermediate;
(ii) removal of unreacted crosslinker from the covalently bound crosslinker intermediate; and
(iii) covalent binding of the crosslinker to the other of the first or second species through a moiety reactive with a second functional group that is the other of the N-hydroxysuccinimide or maleimide functional group.
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Abstract
The present invention describes carbamic acid ester-derived and valeric acid ester-derived polyfunctional cross-linker molecules, and methods for their synthesis and use. The inclusion of polymeric moieties such as poly(alkylene oxide) in the cross-linkers of the present invention can provide advantageous solubility properties in aqueous environments. Such cross-linkers may be used to form conjugates for use in a variety of assay formats.
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Citations
16 Claims
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1. A method of conjugating a first species selected from the group consisting of a protein, a polypeptide, an antibody, a nucleic acid, a small molecule, an aptamer, and a carbohydrate, to a second species selected from the group consisting of a detectable label, a solid phase, a protein, a polypeptide, an antibody, a nucleic acid, a small molecule, an aptamer, and a carbohydrate, the method comprising:
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contacting said first and second species with a crosslinker of the formula;
wherein X is (alkylene oxide)n; n is between about 40 to about 450; and Y and Z are independently arylene or heteroarylene units having 5 or 6 ring atoms, optionally substituted with from 1 to 4 substituents independently selected from the group consisting of C1-6 alkyl straight or branched chain, halogen, trihalomethyl, C1-6 alkoxy, —
NO2, —
NH2, —
OH, —
COOR′
, where R′
is H or lower alkyl, —
CH2OH, —
CONH2, and a linkage to a poly(alkylene oxide) moiety, wherein Z is optionally present;under conditions selected to conjugate said first species to said second species, wherein one of the first or second species becomes covalently bound to said crosslinker through a moiety reactive with an N-hydroxysuccinimide functional group, and the other of the first or second species becomes covalently bound to said crosslinker through a moiety reactive with a maleimide functional group wherein the conjugating step comprises (i) covalent binding of the crosslinker to the first or second species through a moiety reactive with a first functional group that is an N-hydroxysuccinimide or a maleimide functional group, to form a covalently bound crosslinker intermediate;
(ii) removal of unreacted crosslinker from the covalently bound crosslinker intermediate; and
(iii) covalent binding of the crosslinker to the other of the first or second species through a moiety reactive with a second functional group that is the other of the N-hydroxysuccinimide or maleimide functional group. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)
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Specification
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Current AssigneeBiosite Diagnostics Incorporated (Abbott Laboratories)
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Original AssigneeBIOSITE INCORPORATED (Abbott Laboratories)
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InventorsBuechler, Kenneth F., Banaszczyk, Mariusz G., Noar, Joseph Barry
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Primary Examiner(s)Le, Long V.
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Assistant Examiner(s)Haq, Shafiqul
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Application NumberUS11/080,211Publication NumberTime in Patent Office253 DaysField of Search436/533, 436/532, 436/543, 525/532, 525/54.1, 548/534, 548/545, 548/563US Class Current436/533CPC Class CodesC07D 207/46 with hetero atoms directly ...
